2-(5-Carbamoyl-2-fluorophenylamino)-2-(3-ethoxy-4-fluorophenyl)acetic acid → HCID 59479532, compound

HRID 1515522Notes

Reaction equation

HRID 1515522 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:25])=[C:8]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH2:23][CH3:24])[CH:16]=2)[C:12](O)=[O:13])[CH:9]=1)(=[O:3])[NH2:2].Cl.[CH:27]([S:30]([C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40](=[O:44])[N:41]([CH3:43])[CH3:42])=[CH:35][C:34]=1[C@H:45]1[CH2:49][CH2:48][CH2:47][NH:46]1)(=[O:32])=[O:31])([CH3:29])[CH3:28]>>[CH3:43][N:41]([CH3:42])[C:40](=[O:44])[NH:39][C:36]1[CH:37]=[CH:38][C:33]([S:30]([CH:27]([CH3:28])[CH3:29])(=[O:32])=[O:31])=[C:34]([C@H:45]2[CH2:49][CH2:48][CH2:47][N:46]2[C:12](=[O:13])[C@H:11]([NH:10][C:8]2[CH:9]=[C:4]([CH:5]=[CH:6][C:7]=2[F:25])[C:1]([NH2:2])=[O:3])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH2:23][CH3:24])[CH:16]=2)[CH:35]=1

Participants

3

Reactant 2

HCID 594795302-(5-Carbamoyl-2-fluorophenylamino)-2-(3-ethoxy-4-fluorophenyl)acetic acidHCID 68439178HCID 68439178, compound

Product 1

HCID 59479532HCID 59479532, compound

Procedure

Example 33 was prepared according to the general coupling condition using 29A and 31A. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.19 (d, J=6.59 Hz, 3 H) 1.31 (t, J=7.03 Hz, 3H) 1.44 (d, J=6.59 Hz, 3H) 1.68-1.81 (m, 1H) 1.99-2.09 (m, 1H) 2.08-2.19 (m, 1H) 2.40-2.57 (m, 1H) 3.00 (s, 6H) 3.69-3.78 (m, 1H) 3.79-3.89 (m, 1H) 3.90-4.02 (m, 2H) 4.11-4.20 (m, 1H) 5.44 (s, 1H) 5.65 (dd, J=8.35, 5.27 Hz, 1H) 6.80 (d, J=2.20 Hz, 1H) 6.96-7.05 (m, 4H) 7.10-7.19 (m, 1 H) 7.30 (d, J=8.79 Hz, 2H) 7.71 (d, J=8.35 Hz, 1H), LCMS: 672 (M+1).

Workup

  1. customExample 33 was prepared

Sources & evidence

ORD record
ord-56af46daed87416082461ab2884f0e85
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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